benzyl O-[3(R)-acetoxy-2(S)-benzyloxycarbonylamino-1-oxobutyl]-N-trifluoroacetyl-L-serinate → O-[3(R)-acetoxy-2(S)-amino-1-oxobutyl]-N-trifluoroacetyl-L-serine

HRID 2165234Notes

Reaction equation

HRID 2165234 reaction equation
[C:1]([O:4][C@H:5]([CH3:40])[C@H:6]([NH:29]C(OCC1C=CC=CC=1)=O)[C:7]([O:9][CH2:10][C@@H:11]([C:19]([O:21]CC1C=CC=CC=1)=[O:20])[NH:12][C:13](=[O:18])[C:14]([F:17])([F:16])[F:15])=[O:8])(=[O:3])[CH3:2]>[Pd].C(O)(=O)C>[C:1]([O:4][C@H:5]([CH3:40])[C@H:6]([NH2:29])[C:7]([O:9][CH2:10][C@@H:11]([C:19]([OH:21])=[O:20])[NH:12][C:13](=[O:18])[C:14]([F:16])([F:15])[F:17])=[O:8])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 18639967benzyl O-[3(R)-acetoxy-2(S)-benzyloxycarbonylamino-1-oxobutyl]-N-trifluoroacetyl-L-serinate

Product 1

HCID 18640000O-[3(R)-acetoxy-2(S)-amino-1-oxobutyl]-N-trifluoroacetyl-L-serine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of benzyl O-[3(R)-acetoxy-2(S)-benzyloxycarbonylamino-1-oxobutyl]-N-trifluoroacetyl-L-serinate (1.42 g) and 10% palladium on activated carbon (300 mg) in acetic acid (50 ml) was hydrogenated under hydrogen at 40 psi at room temperature for 2 hours. The mixture was filtered with Celite (filter aid, trade mark, made by Nakarai Chemicals) and the filtrate was concentrated. The residue was diluted with water and lyophilized to give O-[3(R)-acetoxy-2(S)-amino-1-oxobutyl]-N-trifluoroacetyl-L-serine.

Workup

  1. filtrationThe mixture was filtered with Celite (filter aid, trade mark, made by Nakarai Chemicals)
  2. concentrationthe filtrate was concentrated
  3. additionThe residue was diluted with water

Sources & evidence

ORD record
ord-5358dee8126f495da56404a8cfc95dd7
Source dataset
uspto-grants-1990_07
Patent number
US04939241

Reaction notes

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